How to Wear Plaid Skirts This Winter

work holiday Christmas party outfit

Plaid skirts play a major role in my fall and winter wardrobe. I break them out in September and keep them in rotation through March. Plaid skirts are ideal for the holidays—nothing is better for Nutcracker performances or cookie exchanges—but also for work and dates.

I have trouble styling plaid skirts because they look either too prim and schoolgirlish or inappropriately sexy. The two best ways I’ve found to balance a plaid skirt are grown-up neutrals for work and metallics and sparkle for play. Below, I share five outfits with plaid skirts for a variety of occasions.

Outfit #1: A Christmas Get-Together With Friends

holiday outfit with houndstooth skirt

This outfit is casual, but still festive and will look great in photos, especially if your friends are as keen on taking photos as mine are! With flats, you’ll be comfortable even if you have to change metro lines to get there, and since you won’t be wearing tights you can comply with any weird “shoes off at my apartment” rules.

Start with this houndstooth miniskirt that I’ve been wearing all fall. I know that houndstooth may not technically be a plaid, but it has the same holiday vibe. This skirt has stripes of burgundy and navy running through it, so I paired it with a comfortable but fitted navy sweater. To keep things well-accessorized and festive, I added silver pointy-toe flats and a crystal statement necklace.

Outfit #2: For Work

work holiday Christmas party outfit

This outfit is a flattering-but-appropriate combination for any fall or winter day at work, and it will also work for an office Christmas party. The top and skirt are lightweight, so it’s perfect for the beginning of December in warmer climates or an extra-warm office. If you need something to wear to a Christmas party, this outfit will work for everything from get-togethers during work to office-appropriate evening soirees.

Start with this fitted black wool pencil skirt in black watch plaid, then tuck in this black blouse, which has an open neckline but doesn’t show cleavage. To make the outfit party-ready, add a pair of fun pumps, like these pink ones, and a sparkly statement necklace. If you work at an uber-conservative office, you can switch out the pink pumps for nude or black ones and add a black blazer.

Outfit #3: Winter Date Night

winter outdoor date outfit

DC has lots of fun winter activities for an outdoor date during December, like Zoolights and the national Christmas tree lighting. After Christmas, most cities still have ice skating rinks or, if you’re averse to spending time outdoors during winter, you can try hot chocolate at different cafes. If you’re going on a cold outdoor date or out getting drinks with friends, this cute and cozy outfit is for you.

This blue plaid miniskirt (the same cut as the houndstooth one above) is preppy and slightly edgy. I added this white cropped sweater, which works with the high-waisted skirt, black tights, black boots, and a faux-leather jacket. I’m wearing combat boots, but for a more classic look you could opt for a pair of black booties.

Outfit #4: Casual Thursday

casual work outfit

We all have Thursdays that we wish were casual Fridays—a Thursday before everyone leaves for Christmas, or one during that gray time of January. Whether you were packing furiously in the morning to leave straight from work for the holidays, or you’re trying to finish up odds and ends of work before you can leave for a long weekend, or you just had a hard time waking up, this outfit is casual but nice and put-together.

I paired this houndstooth pencil skirt (which, yes, is just a longer version of the houndstooth skirt above) with a crisp chambray button-up shirt to bring out the blue stripe in the pattern of the skirt. This pencil skirt can look dowdy on me since I’m petite, and while loafers would be comfortable they make the skirt too “refugee from London during WWII,” so I finished the outfit with nude heels. If you’re traveling after work, change out the skirt and heels for jeans and casual-cute sneakers and throw on an oversized cardigan for a comfortable double-denim travel outfit.

Outfit #5: Holiday Get-Together with Family

Thanksgiving day outfit in the lobby of the Study Hotel

OK, so you’re still in your pajamas, or at least a thermal and sweats, for Christmas morning, but at some point you’ll want to put on real clothes, especially if you’re traveling to see other family members. I covered this festive skirt in my “Preppy Layering for Fall” post, but this is another, more casual way to style it.

I added a patterned button-down, a funky-fun sweater, and comfortable loafers. I’m wearing my pheasant sweater, but a graphic sweater (especially if you have one in white or gray, like this one) would be great too. This is a good way to look festive and comfortable to spend time with your family.

Are you a big fan of plaid skirts for winter? Which of these outfits do you like best? Tell me in the comments!

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